AI Article Synopsis
- Beta-hydroxy acids were chemically reacted with hexafluoroacetone and carbodiimides to create carboxy-activated six-membered lactones efficiently.
- When these lactones reacted with amines, they produced the corresponding amides.
- The study showcases this strategy's applications in creating carboxamides in various conditions, recovering and reusing materials in solid-phase synthesis, and achieving convergent solid-phase peptide synthesis with minimal epimerization.
Article Abstract
beta-Hydroxy acids were reacted with hexafluoroacetone and carbodiimides to give carboxy-activated six-membered lactones in good yields. On reaction with amines, the corresponding amides were obtained. We demonstrate the following applications of this protecting/activating strategy: preparation of carboxamides in solution and on solid phase (both normal and reverse mode); recovery and reuse of the excess material in solid-phase synthesis; and convergent solid-phase peptide synthesis (CSPPS) with peptide segments bearing C-terminal Ser or Thr with very low levels of epimerization (<1%, HPLC).
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| http://dx.doi.org/10.1021/jo7025788 | DOI Listing |
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